[NH2:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]2[C:12]([CH3:14])([CH3:13])[O:11][B:10]([OH:15])[C:9]=2[CH:16]=1)([CH3:4])[CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Cl:50][C:51]1[CH:52]=[C:53]([C:59]2([C:76]([F:79])([F:78])[F:77])[O:63][N:62]=[C:61]([C:64]3[N:65]4[C:69]([C:70]([C:73](O)=[O:74])=[CH:71][CH:72]=3)=[CH:68][CH:67]=[CH:66]4)[CH2:60]2)[CH:54]=[C:55]([Cl:58])[C:56]=1[Cl:57]>C1COCC1.CC(=O)OCC>[OH:15][B:10]1[C:9]2[CH:16]=[C:5]([C:2]([NH:1][C:73]([C:70]3[C:69]4[N:65]([CH:66]=[CH:67][CH:68]=4)[C:64]([C:61]4[CH2:60][C:59]([C:53]5[CH:54]=[C:55]([Cl:58])[C:56]([Cl:57])=[C:51]([Cl:50])[CH:52]=5)([C:76]([F:79])([F:77])[F:78])[O:63][N:62]=4)=[CH:72][CH:71]=3)=[O:74])([CH3:4])[CH3:3])[CH:6]=[CH:7][C:8]=2[C:12]([CH3:14])([CH3:13])[O:11]1To a solution of 6-(2-aminopropan-2-yl)-3,3-dimethylbenzo[c][1,2]-oxaborol-1(3H)-ol (100 mg), HATU (277 mg, 0.73 mmol) and DIPEA (0.2 mL, 1.1 mmol) in THF (5 mL) can be added 5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-8-carboxylic acid (0.37 mmol). The reaction mixture can be stirred at rt overnight. EA can be added and the mixture can be washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue can be purified by prep-HPLC to give the final title compound.
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